EP0780418A3 - Triamines and a process for their preparation - Google Patents
Triamines and a process for their preparation Download PDFInfo
- Publication number
- EP0780418A3 EP0780418A3 EP96119773A EP96119773A EP0780418A3 EP 0780418 A3 EP0780418 A3 EP 0780418A3 EP 96119773 A EP96119773 A EP 96119773A EP 96119773 A EP96119773 A EP 96119773A EP 0780418 A3 EP0780418 A3 EP 0780418A3
- Authority
- EP
- European Patent Office
- Prior art keywords
- total weight
- hydrolysis
- content
- crosslinker
- preparations
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title abstract 7
- 239000004971 Cross linker Substances 0.000 abstract 4
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- -1 3-amino-4-methylphenyl Chemical group 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 abstract 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229920000768 polyamine Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/508—Amines heterocyclic containing only nitrogen as a heteroatom having three nitrogen atoms in the ring
- C08G59/5086—Triazines; Melamines; Guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Beschrieben werden flüssige Polyaminvernetzer-Zubereitungen auf der Basis von trimerisiertem 2,4- und/oder 2,6-Toluylen-diisocyanat unter Ausbildung einer Isocyanuratstruktur und Hydrolyse der Isocyanatgruppen zu Aminogruppen. Die neuen Vernetzer-Zubereitungen sind gekennzeichnet durch einen Gehalt von 40 bis 80 % des Gesamtgewichts des Feststoffanteils der Vernetzer-Zubereitung an nicht weiter kondensiertem 1,3,5-Tris-(3-amino-4-methyl-phenyl,2-methyl-3-amino-phenyl)-isocyanurat (I) und durch einen Gehalt von höchstens 1,0 % des Gesamtgewichts der Vernetzer-Zubereitungen an Toluylen-2,4- bzw. -2,6-diamin (III). Zur Herstellung wird Toluylen-diisocyanat unter Ausbildung der Isocyanuratstruktur trimerisiert, bis 10 bis 25 % der NCO-Gruppen umgesetzt worden sind. Danach wird das nicht kondensierte Toluylen-diisocyanat abdestilliert, das dabei entstehende Sumpfprodukt unmittelbar in einem Lösungsmittel A aufgenommen und die dabei entstehende 30 bis 70 gew.-%ige Lösung der Hydrolyse in Wasser/N,N-Dialkyl-carbonsäureamid in Gegenwart einer katalytischen Menge eines basischen Katalysators eindosiert. Nach der Hydrolyse werden die Vernetzer-Zubereitungen durch anteiliges Abdestillieren von Lösungsmitteln und Zugabe eines Lösungsmittels B auf einen Feststoffanteil von 35 bis 60 % des Gesamtgewichts der Zubereitung eingestellt. Liquid polyamine crosslinker preparations based on are described trimerized 2,4- and / or 2,6-tolylene diisocyanate to form a Isocyanurate structure and hydrolysis of the isocyanate groups to amino groups. The new crosslinker preparations are characterized by a content of 40 to Not 80% of the total weight of the solids content of the crosslinking agent preparation further condensed 1,3,5-tris (3-amino-4-methylphenyl, 2-methyl-3-aminophenyl) isocyanurate (I) and by a content not exceeding 1.0% of the Total weight of the crosslinker preparations of tolylene-2,4- or -2,6-diamine (III). Toluylene diisocyanate is produced with the formation of Isocyanurate structure trimerized until 10 to 25% of the NCO groups reacted have been. Then the uncondensed tolylene diisocyanate distilled off, the resulting bottom product immediately in one Solvent A added and the resulting 30 to 70 wt .-% Solution of hydrolysis in water / N, N-dialkyl-carboxamide in the presence of a dosed catalytic amount of a basic catalyst. After hydrolysis become the crosslinker preparations by partially distilling off solvents and addition of a solvent B to a solids content of 35 to 60% of the total weight of the preparation set.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19548026 | 1995-12-21 | ||
| DE19548026A DE19548026A1 (en) | 1995-12-21 | 1995-12-21 | Polyamine crosslinking agent preparation and its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0780418A2 EP0780418A2 (en) | 1997-06-25 |
| EP0780418A3 true EP0780418A3 (en) | 1997-07-09 |
Family
ID=7780941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP96119773A Withdrawn EP0780418A3 (en) | 1995-12-21 | 1996-12-10 | Triamines and a process for their preparation |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5705594A (en) |
| EP (1) | EP0780418A3 (en) |
| JP (1) | JPH101533A (en) |
| KR (1) | KR970042651A (en) |
| CA (1) | CA2193321A1 (en) |
| CZ (1) | CZ378996A3 (en) |
| DE (1) | DE19548026A1 (en) |
| HU (1) | HU217848B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2804112B1 (en) * | 2000-01-20 | 2004-04-30 | Rhodia Chimie Sa | PROCESS FOR OBTAINING LOW-COLORED BRANCHED ISOCYANATE (S) CYCLOTRIMERS AND COMPOSITION THEREOF |
| WO2001053277A1 (en) * | 2000-01-20 | 2001-07-26 | Rhodia Chimie | Method for obtaining slightly coloured branched polyisocyanate(s), and resulting composition |
| JP5069494B2 (en) * | 2007-05-01 | 2012-11-07 | ＡｚエレクトロニックマテリアルズＩｐ株式会社 | Water-soluble resin composition for forming fine pattern and fine pattern forming method using the same |
| WO2018076199A1 (en) * | 2016-10-26 | 2018-05-03 | Covestro Deutschland Ag | Tdi based low-viscosity polyisocyanates with isocyanurate groups |
| WO2018076198A1 (en) * | 2016-10-26 | 2018-05-03 | Covestro Deutschland Ag | Tdi based polyisocyanate mixture with a high solids content |
| KR20260009351A (en) * | 2023-05-12 | 2026-01-19 | 헬리오스 코팅스, 인크. | Low-temperature curing adhesion promoters and primers for substrates |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2801244A (en) * | 1956-07-10 | 1957-07-30 | Du Pont | Trifunctional isocyanate trimers |
| DE3227219A1 (en) * | 1982-07-21 | 1984-02-02 | Bayer Ag, 5090 Leverkusen | ONE-STEP PROCESS FOR PRODUCING POLYAMINES FROM NCO-PRAEPOLYMERS, POLYAMINS AND THE USE THEREOF FOR PRODUCING POLYURETHANES |
| EP0271772A2 (en) * | 1986-12-15 | 1988-06-22 | Siemens Aktiengesellschaft | Epoxy resin molding compounds |
| EP0274646A1 (en) * | 1986-12-15 | 1988-07-20 | Siemens Nixdorf Informationssysteme Aktiengesellschaft | Process for the preparation of prepregs, and their use |
| EP0384939A1 (en) * | 1989-03-03 | 1990-09-05 | Siemens Aktiengesellschaft | Epoxy resin moulding compositions |
| EP0384940A1 (en) * | 1989-03-03 | 1990-09-05 | Siemens Aktiengesellschaft | Epoxy resin compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2551634C3 (en) * | 1975-11-18 | 1980-07-17 | Bayer Ag, 5090 Leverkusen | Process for the preparation of polyisocyanates containing isocyanurate groups |
| DE3035639A1 (en) * | 1980-09-20 | 1982-04-29 | Bayer Ag, 5090 Leverkusen | NEW DI- AND POLYAMINE, METHOD FOR THEIR PRODUCTION, AND THEIR USE |
-
1995
- 1995-12-21 DE DE19548026A patent/DE19548026A1/en not_active Withdrawn
-
1996
- 1996-12-10 EP EP96119773A patent/EP0780418A3/en not_active Withdrawn
- 1996-12-16 US US08/767,564 patent/US5705594A/en not_active Expired - Fee Related
- 1996-12-18 JP JP8353949A patent/JPH101533A/en active Pending
- 1996-12-18 CA CA002193321A patent/CA2193321A1/en not_active Abandoned
- 1996-12-20 HU HU9603581A patent/HU217848B/en not_active IP Right Cessation
- 1996-12-20 KR KR1019960069188A patent/KR970042651A/en not_active Withdrawn
- 1996-12-20 CZ CZ963789A patent/CZ378996A3/en unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2801244A (en) * | 1956-07-10 | 1957-07-30 | Du Pont | Trifunctional isocyanate trimers |
| DE3227219A1 (en) * | 1982-07-21 | 1984-02-02 | Bayer Ag, 5090 Leverkusen | ONE-STEP PROCESS FOR PRODUCING POLYAMINES FROM NCO-PRAEPOLYMERS, POLYAMINS AND THE USE THEREOF FOR PRODUCING POLYURETHANES |
| EP0271772A2 (en) * | 1986-12-15 | 1988-06-22 | Siemens Aktiengesellschaft | Epoxy resin molding compounds |
| EP0274646A1 (en) * | 1986-12-15 | 1988-07-20 | Siemens Nixdorf Informationssysteme Aktiengesellschaft | Process for the preparation of prepregs, and their use |
| EP0384939A1 (en) * | 1989-03-03 | 1990-09-05 | Siemens Aktiengesellschaft | Epoxy resin moulding compositions |
| EP0384940A1 (en) * | 1989-03-03 | 1990-09-05 | Siemens Aktiengesellschaft | Epoxy resin compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2193321A1 (en) | 1997-06-22 |
| HUP9603581A3 (en) | 1998-06-29 |
| EP0780418A2 (en) | 1997-06-25 |
| JPH101533A (en) | 1998-01-06 |
| US5705594A (en) | 1998-01-06 |
| HU217848B (en) | 2000-04-28 |
| KR970042651A (en) | 1997-07-24 |
| DE19548026A1 (en) | 1997-06-26 |
| HUP9603581A2 (en) | 1997-10-28 |
| CZ378996A3 (en) | 1997-08-13 |
| HU9603581D0 (en) | 1997-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
| AK | Designated contracting states |
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| AK | Designated contracting states |
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| 17P | Request for examination filed |
Effective date: 19980109 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| 18W | Application withdrawn |
Withdrawal date: 20001018 |